5638 S WOODLAWN Avenue
Chicago, IL, 60637
$3,100,000
6 Beds
9 Baths
8,000 SqFt
0 Acres
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$3,100,000
5638 S WOODLAWN Avenue
Chicago, IL, 60637
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5638 South Woodlawn Avenue represents a unique opportunity to own a piece of Chicago’s architectural heritage. Designed in 1911 by celebrated architect Howard Van Doren Shaw for publishing executive Henry Hoyt Hilton and his wife Charlotte, this three-story Federal-style residence embodies timeless elegance and thoughtful design. Shaw, later honored with the American Institute of Architects’ Gold Medal, was renowned for his refined use of symmetry, proportion, and classical detail-hallmarks clearly evident here. Meticulously restored and updated, the massive 8,000-square-foot home blends original grandeur with modern luxury. Historic details – majestic fireplaces, gleaming hardwood detailing, and an elegant main staircase-are complemented by a new chef’s kitchen, renovated baths, a reimagined third-floor great room, as well as the practical including a spacious laundry. The lower level adds a workout room, media room, and abundant storage. With six bedrooms, five full ensuite baths, and three half baths, this residence offers both scale and versatility for modern living. Set in the heart of the University of Chicago community, this historic property is as livable as it is significant – a piece of architectural history, seamlessly blending Shaw’s timeless vision with contemporary elegance in one of Chicago’s most celebrated neighborhoods.

Property Details

Price:
$3,100,000
MLS #:
MRD12446282
Status:
Active
Beds:
6
Baths:
9
Type:
Single Family
Neighborhood:
chihydepark
Listed Date:
Sep 15, 2025
Finished Sq Ft:
8,000
Year Built:
1911
Chi – Hyde ParkChihydeparkRay Elementary SchoolCanter Middle SchoolKenwood Academy High School

Schools

School District:
299
Elementary School:
Ray Elementary School
Middle School:
Canter Middle School
High School:
Kenwood Academy High School

Interior

Bathrooms
6 Full Bathrooms, 3 Half Bathrooms
Cooling
Wall Unit(s)
Fireplaces Total
3
Heating
Natural Gas
Laundry Features
In Unit, Laundry Chute, Sink

Exterior

Architectural Style
Traditional
Construction Materials
Brick
Parking Features
Off Alley, On Site, Owned
Parking Spots
3

Financial

HOA Frequency
Not Applicable
HOA Includes
None
Tax Year
2023
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Debra Dobbs is one of Chicago’s top realtors with more than 41 years in the real estate business.

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Current real estate data for Single Family in Chicago as of Sep 16, 2025
3,099
Single Family Listed
69
Avg DOM
227
Avg $ / SqFt
$551,250
Avg List Price

Community

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Property Summary

    5638 S WOODLAWN Avenue Chicago IL is a Single Family for sale in Chicago, IL, 60637. It is listed for $3,100,000 and features 6 beds, 9 baths, and has approximately 8,000 square feet of living space, and was originally constructed in 1911. The current price per square foot is $388. The average price per square foot for Single Family listings in Chicago is $227. The average listing price for Single Family in Chicago is $551,250. To schedule a showing of MLS#mrd12446282 at 5638 S WOODLAWN Avenue in Chicago, IL, contact your Compass / The Debra Dobbs Group agent at 3123074909.
5638 S WOODLAWN Avenue
Chicago, IL